4-Iminocyclobutenones: Synthesis and Building-Blocks of Aminohydroquinones and Annulated Quinolines

Ernst Schaumann, Gerrit Oppermann, Michael Stranberg, Harold Moore, Gunadi Adiwidjaja
2010 Synthesis (Stuttgart)  
Two methods are presented for the synthesis of the title compounds starting from cyclobutenediones: an alkoxide substitution approach and a Staudinger reaction. Unsaturated lithiumorganyls may be added to the remaining carbonyl group and on heating lead to ring enlargement in a cascading process. 4-Alkenyl or 4-aryl derivatives yield aminophenols ornaphthols; 4-alkynyl compounds give cyclopenta-annulated quinolines. © Georg Thieme Verlag Stuttgart. eScholarship provides open access, scholarly
more » ... access, scholarly publishing services to the University of California and delivers a dynamic research platform to scholars worldwide. Abstract: Two methods are presented for the synthesis of the title compounds starting from cyclobutenediones: an alkoxide substitution approach and a Staudinger reaction. Unsaturated lithiumorganyls may be added to the remaining carbonyl group and on heating lead to ring enlargement in a cascading process. 4-Alkenyl or 4-aryl derivatives yield aminophenols or -naphthols; 4-alkynyl compounds give cyclopenta-annulated quinolines.
doi:10.1055/s-0029-1218767 fatcat:lxu7a2ukszcrndzesrsiezvydi